Jeff Tweedy declared himself a songwriter at 7 years old. Fifty-one years later, most would say he’s fulfilled his prophecy. Tweedy has helmed Wilco, hailed by many as one of the last great American rock bands, for 30 years. And for the past seven, he’s slowly amassed a solo catalog of four albums. His fifth, a gargantuan triple LP titled Twilight Override, is due out September 26 via dBpm.

“A 7-year-old me is probably a better songwriter than I am,” Tweedy tells me over the phone, reflecting on his confident younger self. “I’m still trying to take advice from that version of me, and I think that’s what everybody trying to make something creative is attempting to do: turn off their default mode and become as imaginative as they were when they were kids.”

Twilight Override often finds Tweedy exploring alternate iterations of himself, real and imagined. “There’s a version of me that hangs out in parking lots… He has a car, the hood is popped / Talking to some other mes I don’t recognize,” he says early on the album, in a rare spoken-word passage that rides a slow-swinging instrumental. “But this guy / This show-off showing off / Kinda rules / He obviously knows a lot about cars.”

It’s amusing to picture the soft-spoken Tweedy as a macho car guy, but the next line lends an unexpected poignancy to the image. “I / Or the me I most am / Drives by in the backseat of my parents’ car / Wondering what it’s like / To care that much about chrome / Sincerely.” 

The tableau comes from a real childhood memory, he says, of the drive-in Steak ’n Shake near his house growing up, the kind of place where the waiters came out to your car with a tray. It was the main hangout for hot-rod guys in Belleville, Illinois, a small former industrial hub about half an hour south of St. Louis. The towns around it are rural, so many of Tweedy’s classmates were bussed in from farms. 

On the straight-ahead folk rock jam “Forever Never Ends,” he sings about the time his car broke down on the way back from prom to his date’s house “in the middle of nowhere,” Peppermint Schnapps on his breath and “vomit in the frozen grass” as the cops rolled by but didn’t stop. Again, he’s writing from memory. “I really did throw a rod in a Volkswagen Rabbit,” he says—hot-rod-guy speak for when the rod that connects the piston to the crankshaft breaks off of the engine. Tweedy was driving without oil, he says, and the piston went all the way through the hood. In other words, bad news.

Elsewhere, Tweedy gets headier, reaching further back into an imagined past. On album opener “One Tiny Flower,” for instance, he works from the dubious concept that, at some point in history, “somebody must have whimsically jumped over a flower instead of stepping on it, and tripped and fell to their death,” he explains. “It’s the thought experiment of lying there dying after ostensibly being so loving of nature that you avoid stepping on a tiny little flower. You’re like, ‘I must be the only person that ever jumped over a tiny flower and died.’”

Dark humor is one way Tweedy copes with the components he elegantly sums up with the word “twilight”: the descent of the American Empire into fascism, the seemingly imminent collapse of civilization at large, his own approaching old age—“a bottomless basket of rock bottom,” he writes in Twilight Override’s bio. “It’s like that old joke about the restaurant,” he tells me. “‘The food’s awful here… And such small portions.” Essentially, life sucks, and there’s too little of it.

But his new album is by no means cynical. As in his work with Wilco, his writing is wry but ultimately earnest, wringing hope and wisdom out of the bleak and the banal. On “Better Song,” he sings about his burning desire to create constantly, to push himself harder even after all these years—the type of desire that leads an artist with absolutely nothing to prove to make a 30-track solo album. “It’s a sort of reaching out and wanting to find connection and warmth,” he says. “That’s one of the embarrassing things about getting on stage; everybody immediately knows something pretty deep about you: that you have a need for approval and love.” Not many performers would admit that.

Then there’s “Lou Reed Was My Babysitter,” in which a Velvet Underground-indebted instrumental undergirds a plainspoken message—“Rock ‘n’ Roll is dead, but the dead don’t die.” The song’s verses describe uncontrollable urges: “I wanna sweat next to you.” “I want you to dance into me.” “I want you to blow smoke in my eyes.” All the things you want when you step into the beer-stained rock club or the smoke-stained house show, if you’re doing it right.

Lou Reed was famously sharp-edged and could come off deeply cynical at times, but he was a fervent promoter of experimental art until his last breath, and his own work was raw and shockingly vulnerable at its core. “The Velvet Underground was one of my main guiding principles of radically individuated self expression,” Tweedy says. “[Reed was] encouraging other people to be themselves and—in a weird, acerbic way—punishing people into not wanting to be anybody else.”

Tweedy’s self-expression is less caustic than Reed’s, but the influence is evident in the way he fearlessly welcomes us into the inner workings of his mind. On Twilight Override’s title track, he admits he used to wish for a broken arm so his classmates could sign his cast.  “I’ll need to find a new past,” he sings. It’s not a particularly dark secret, but it’s an elegant example of his rare balance of self-awareness and self-acceptance. 

Vulnerability and self-knowledge breed empathy, too. “It’s hard to stay in love / With everyone,” Tweedy sings on “Enough,” Twilight Override’s closer. That’s the ultimate goal, though. “Give yourself permission to be yourself, and in doing so encourage other people to give themselves permission,” he says. “I think that’s the great promise of rock ’n’ roll music: It’s very unserious and it’s very dumb, and at the same time it’s deadly important. I believe this with all my heart at this point in my life—that it’s not nothing, that it saves people.

“I turned on my radio when I was five years old, and my life was saved by rock ’n’ roll,” he concludes, interpolating his artistic role model, his spiritual guide, and, in a new past of his own creation, his babysitter. “I’m not the one who said that.”

Photographed by Jakob Favela

Styled by Camille Ries

Written by Raphael Helfand

Grooming: Gina Barrington at The LAB Artist Agency 

Producer: Bree Castillo